Author: johnmvalentine

My son, due to be born any day now (goodbye sleep!), will never have to sit through grueling summer driver’s education classes or feign the ability to parallel park while a stranger gripping a greasy clipboard and making weird wheezing noises glances warily from the passenger seat.

Yes, there will be cars on the road. No, humans won’t be driving them.

Better yet, the majority of humans will cease to own cars in the next ten years. That means no more leases, car loans, car insurance, two, three, and four-car households, shoveling remnants of the latest snowstorm off the roof, waiting in line at Jiffy Lube for the 5,000-mile oil change, haggling with the car salesman for a below invoice quote, or getting towed after parking in the handicap spot. How can this be possible?

Artificial Intelligence, Robotics, and Networks

Two separate but conjoined movements are in a collision course to change transportation forever: 1) Autonomous Vehicle Technologies and 2) Distributed Networks of On-Demand Transportation Services.

If you don’t think autonomous car technology isn’t going to control all transportation in the future, take a look at what Audi, Tesla, BMW, Waymo, Uber, Otto, Swift Navigation, and hundreds of other startups and established players are building. Recently, Tesla released a software update that allows owners to summon their parked cars to them and cruise unassisted on the highway at 80 MPH. Our self-driving overlords are on the doorstep.

The rush to achieve Level 5 automobile autonomy is the heart-pounding, bated-breath, trucks-full-of-cash type of fun, but in a few short years this technology will be ubiquitous. The true winner in the transportation industry will be the company that can merge autonomous vehicle technology with the largest network of available vehicles and consumers. Currently, Uber and Lyft have a stronghold on the networked cars market, and their value will increase substantially in the next decade. Lyft’s recently-announced partnership with Waymo is a potentially lethal combination, and you might expect Tesla and Uber to join forces soon. Long-term competition in this space won’t likely come from upstarts like Fasten; they will come from the auto giants who will soon put their entire market value on the line to preserve their suffocating businesses.

Preparing for the Future, Today

Why is Tesla hitting the gas to launch the Model 3 mass-market car as quickly as possible? Because Tesla is subversively asking consumers to finance its autonomous vehicle fleet. Some Tesla owners are already making $1,000+ per month renting to others on car-sharing sites like Turo. In a few years, Tesla will send every customer an email giving them the ability to make extra money by allowing their vehicle to run autonomously on the Tesla network when they’re not using it. When these customers realize the on-demand option is better for their needs and their wallet, they will let their vehicle run on the network almost 100% of the time and subsequently refrain from buying another car ever again.

The New York Times just published an article on the lack of customer adoption of car-sharing models, but the reasons it cites, insurance nightmares, driver negligence, and accidents, can be at least partially solved through vehicle autonomy. Assuming driver-less vehicles become safer than cars with human drivers, the driver negligence and accident risks are minimized.

Reforming Urban Areas

A car sitting idle in a parking lot or garage is inefficient and wasteful. In fact, Fortune reported last year that today’s cars are parked 95% of the time. If all vehicles were operating at near 100% utility, all transportation needs in the United States would be satisfied with 5-10% of cars currently in operation. The death of many large automakers is nigh unless consumers use 5-10x more transportation than they do today, which is unlikely.

If you look at a satellite image of downtown Atlanta, you can just about make out every one of its 93,000 parking spaces, most of which sit unoccupied most of the time. A car is not useful while sitting idle in a parking lot or garage. Optimizing transportation and reducing the number of total cars produced allows cities to reclaim many of their parking lots and garages and redesign downtown.

New Revenue Models

Get ready to start paying for transportation like we currently do mobile phone plans. Instead of choosing between the 4GB, 8GB, or 16GB plans at Verizon, you will choose between the 250, 500, or 1,000 miles per month transportation plans, with a specified number of built-in “rush hour” miles. Just as adding additional lines drives the marginal added cost lower, so does adding additional family members to your transportation plan.

Unused miles will rollover, and you can accumulate mileage for that cross-country trip you were planning with dad.

Auto Industry Upheaval

In 2016, automotive manufactures produced over 250 vehicle models, up from 210 in 2000. Choosing a vehicle to purchase or lease is akin to walking down a cereal aisle and choosing the type of cereal you’re going to eat for the next 5 years. It’s a big commitment, with big dollars attached. When life circumstances change, such as a move to a big city where a car isn’t needed or the birth of a child, so do transportation and space requirements. Networks of autonomous vehicles can immediately react to each family’s evolving transportation needs.

There are over 2 billion smartphones in use worldwide, and over 90% run on Android or iOS. While there are hundreds of different models, the Top 10 smartphones dominate market share. The future of transportation will sport no greater than ten vehicle models. Just as originality in the age of smartphones has evaporated (I don’t care that over half my colleagues have the same iPhone 7 as me), so will the need to have hundreds of car models. A quick poll of my friends reveals none of them care which make and model UberX they hop into — they simply want the fastest, cheapest method of getting from Point A to Point B. Many automobile manufacturers will go out of business, and the remaining few will struggle to find profit as a mere commodity.

Always Watching

Wouldn’t it be great if Uber knew exactly when you needed a car? That future isn’t far off, as your Google Calendar will sync to the transportation network so it can anticipate when you’ll need transportation and where you intend to go. If your Google calendar shows a 30-minute gap between meetings and Uber’s network detects a crash on the normal travel route, it may send a text message suggesting you leave 10 minutes early to arrive at the second meeting on-time. The network will automatically recognize you moving to the elevators and make sure a car is waiting for you on the curb. No more opening an app to request transportation. No more waiting. Brace yourself for real-time, reactive transportation that thinks so you don’t have to.

The Auto Insurance Industry Expires

Differentiated data is key to finding success in the auto insurance industry. Vehicle telematics plug-ins have been a relatively easy way for insurance companies to better track your driving behavior, but they have exponentially less data than the automobile manufacturers. The elimination of human error (fewer accidents) from autonomous vehicle technology and an increase in the number and quality of sensors will decrease the cost of insurance and likely cause manufacturers or technology providers to bear the insurance costs themselves.

Autonomous driving will become a major platform that will spawn a new generation of innovators with ideas that will impact the world. Incumbents and disruptors alike need to position themselves as close to the consumer as possible, collecting data points that anticipate movement, behavior, and preferences. Is your company girding for the new world?

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I winced at the unfurled scrap paper sitting menacingly in the palm of my hand. My 2016 goals, splayed out for the requisite self-flagellation. At the end of each year, I write down one personal, professional, and financial goal for myself to tackle over the next twelve months. For 2016, my professional goal was to launch my own podcast on early stage startups. I crumpled up the slip of paper and tossed it into the trash bin across my bedroom. Maybe next year.

The Epiphany

“I really should start a podcast.” I can’t count how many people have heard me utter this sentence. When I picked up my pen last month to write goals for 2017, starting a podcast was absent — I triumphantly told my co-workers the day before that “I’m starting a podcast.” The pressure was on.

Step 1: Picking a Topic [10 Minutes]

It doesn’t make much sense to mimic the subject of an already successful podcast, so I took inventory of what I really enjoyed talking about and what was missing in the podcast ecosystem. I quickly realized the subjects of most entrepreneurship pods were leaders who exited massive companies or had major successes — not the innovators I ran into every day fighting tooth and nail for their next client, wooing potential co-founders, and criss-crossing the country for their next twelve months of runway. Having worked for a number of startups myself, I recognized the gap in conversation lay with the major decision points for early stage entrepreneurs. These conversations could serve as guidance for those thinking about starting a business themselves.

I locked in on 30-minute interviews, published each week on Monday, with founders of Seed and Series A startups. The initial focus would be on Boston, the innovation ecosystem I live and breathe, later expanding to founders across the country. Thirty minutes seemed like enough time to go deep into their challenges and successes without boring the listener.

Step 2: Naming the Podcast [10 Minutes]

I appreciate podcasts like Tech in Boston and Startup Boston Podcast for their focus on one city, but it limits the size of their audience as out-of-staters may be discouraged from listening because of the podcast’s title. To allow for a national audience, I decided to title the podcast “Early Stage.” Short, immediately recognizable, and specific. I did a podcast search to make sure the name hadn’t been taken already, and I couldn’t find anything. Pure gold.

Step 3: Designing the Logo [1 Hour]

While you can’t judge a podcast by its cover, the audience’s natural instinct is to make snap judgements on a podcast from the quality of the cover art. Having zero experience designing logos, I needed help. I asked my colleague Erika for some help over the holidays, and she produce two great options. Most podcasts in the iTunes “New and Noteworthy” section sported large words and vivid colors. Conversely, many of the top podcasts in the business, management, and finance sections focused on a photo of the host and the podcast’s title. After quickly polling a dozen friends, the photo and title option was the unanimous choice for its personal nature. Beautiful logo, check.

Step 3: Buying Audio Equipment [30 Minutes]

Audio equipment is a tough one. I would have loved to make use of the beautiful new PRX Podcast Garage, but they aren’t open on the weekends. I could have grabbed my colleagues Gonzalo and Jeff so I could mic up the participants like a pro, but I wanted a solution that didn’t rely on others constantly helping me out. Blue Audio manufactures great USB microphones, and I bought a couple Snowballs [and picked up a Yeti after the fact]. After pairing those two up with a mic lent to me by a friend, I was ready for showtime.

Step 4: Wooing Your First Podcast Guest [10 Minutes]

Deciding who to bring on as your first guest is pivotal. They have to be likable and fun to talk to, but also full of intrigue and experience from their startup journey. Having spent quality time with over 200 startups since I started at MassChallenge made the decision difficult, and I chose Patrick Boyaggi and Mike Tassone from RateGravity. Coincidentally, the startup just got featured in Bostinno’s “17 Startups for Watch in 2017” list — guess I picked a good one! I respect the guys a ton from interacting with them on a daily basis, and they had just launched their platform in beta, added a couple team members, and finished up their first big funding round. These milestones provided great conversation fodder. If you have any recommendations for startups to host for future episodes, please send me a note!

Step 5: Researching Discussion Questions [2 Hours]

In order to help the conversation flow smoothly, I did a ton of online research into RateGravity and its founders, jotting down notes and organizing my questions under 5 main categories: 1) Elevator Pitch, 2) Origin Story, 3) the Leap, 4) Path Through the Innovation Ecosystem, and 5) Business Deep Dive and Traction. I also wrote out two pages to read at the beginning of the podcast to set the stage for the first conversation and those that will follow. After we stopped recording, both Mike and Patrick complimented my preparation. The research step is critical for anyone about to launch a podcast — quality of content matters most.

Step 6: It’s Go Time! [1 Hour]

With notes in hand, microphones in place, GarageBand fired up on the Mac, audio already tested, and the subjects of my first podcast episode sitting across the table from me in a conference room, I was ready to roll. To help Mike and Patrick feel at ease, we started with small talk to warm them up before hitting record. Thirty minutes flew by as we delved into RateGravity’s elevator pitch, the moment they knew it was time to leave their jobs at Leader Bank, the challenge of adding a technical co-founder, pitching the startup to their wives, building the platform, and beta testing with their first hundred clients. After recording about 40 minutes of reel, I clicked the red stop icon, thanked the guys profusely, and went home to my editing room — a comfy couch.

Step 5: Editing the Audio [4 Hours]

My colleague Jibran told me the best free starter editing platform was Audacity, and he were right. After reviewing the manual wiki, it didn’t take long to understand the basics and get to work chopping the audio. Because I wanted the conversation to feel as raw and unedited as possible, I didn’t cut out more than one minute of content. I was embarrassed to listen to the first 2 minutes, which were full of ‘um’ and ‘uh.’ Using the delete function, some of the longer audible pauses at the beginning of the podcast were removed. I got more comfortable as time went on, and my speaking style started to flourish.

There were two mistakes made during recording that lowered the audio quality. First, I didn’t make sure my guests were positioned super close to the microphone. This caused their voices to be much lower than mine, making the recording more difficult to edit. Second, the sensitive microphones picked up the buzz of the air conditioner above our heads, causing a dull noise throughout the audio. I’ll definitely remedy those problems for episode 2. Audacity’s leveling, compression, amplify and normalize effects helped me equalize the voices on the recording, but I was never able to get the volume to the optimum level. To my listeners: sorry if you have to crank up the volume for episode one!

Step 6: Deciding on a Host and Setting up the RSS Feed [1 Hour]

iTunes doesn’t host podcasts, and there are a ton of opinions on which host to use. Libsyn is popular, but I used SoundCloud because I’m already familiar with the UI. My podcast logo served as the cover photo, and I filled in the blanks in the settings page. I then uploaded the track and added a title, category, and episode description. Next, I went through the steps to get verified on Podcast Connect. After iTunes, I tacked on Stitcher and TuneIn for good measure. While iTunes sees over 80% of podcast listenership, it is important to allow anyone to avail of my podcasting experiment.

Lessons Learned

Starting a podcast has been such a fun journey, re-igniting a love for trying new things and iterating over time to drive improvements. Expect one new episode every Monday morning. Expect the audio to become more crisp and clear with each week. Expect my questions to get more creative and conversations to slip down crazy rabbit holes. Expect me to do my very best, because that’s what I expect of myself.

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“Stop the Car!”

A casual drive down a leafy road in rural Lincoln, RI, was brutally interrupted by my wife’s plea. “There should be a cemetery over on the left. Just pull over right there and wait in the car while I investigate.” I didn’t know whether she was ghost hunting, trying to solve the murder mystery from last night’s evening news, or seeking out the gravestone of a long lost relative. Turns out it was none of those…she was picking up more Poke balls.

Madness

As I watched her dash out of sight, a couple neighborhood kids appeared where she disappeared. After an enthusiastic high-five, the pair checked their phones again and took off jogging down the street. When Michelle returned to the car, I asked what the kids were doing in the cemetery. She asked them the same thing, and they replied, “gotta catch’em all!”

How could the newly-released Pokemon Go have motivated such an unlikely smattering of people to seek out a random cemetery on a rural road…just to earn progress in a mobile app? My humor turned to wonder as I crossed paths, while walking the dogs, with groups of people playing the game: collecting Pokeballs, capturing dozens of Pokemon, and eventually battling each other in PokeGyms. Around 9pm last night, I was walking down a trail with Michelle when a fit 30-something man dashed out of MetroRock, a nearby climbing gym, screaming, “have you seen Krabby? I know he’s around here somewhere!” This is not simply a cute children’s game; people of all ages are getting in on the action.

I’ve seen everyone from parents pushing a stroller to groups of Marines out playing #PokemonGO. It really feels like a cultural phenomenon

Behavior Modification

For the uninitiated, Pokemon Go is a free-to-play augmented reality (AR) game for iOS and Android that allows players to capture, battle, train, and trade virtual Pokemon that appear throughout the real world. Using a smartphone camera, players scan the real world and happen upon hundreds of little creatures, some of which are common and others that are incredibly rare. Water-related Pokemon can be found near streams, rivers, and oceans, and Pokemon bird-like creatures can be found near parks. The most fascinating element of Pokemon Go gameplay is its ability to truly change real-world behavior en masse. This has been one of the ultimate, but until now unrealized, aims of AR. To-date, AR projects have been limited in scope, and many of their most effective applications resided in industry. With the debut of Pokemon Go, hundreds of millions of people around the world are having fun with an easy-to-learn, engaging example of AR.

The app is helping people rediscover abandoned elements of their community…

#PokemonGO is the first thing that’s willingly got me to go into a church in about 10 years.

This Should Have Been Foursquare

Remember SoLoMo (Social, Location, Mobile)? Foursquare Loopt, Whrrl, and SCVNGR all took shots at helping users better interact with the world around them. Checking in, taking photos, earning free appetizers and badges, and doing challenges never hit the mainstream until this weekend. Remember Foursquare Super Swarms? Foursquare’s badges and check-in specials have now given way to placing lures in your business to drive customer traffic. Assuming Niantic builds out venue tools, expect engagement to rise in places you go everyday.

What’s Next?

Pokemon Go’s success will open the eyes and unlock the brains of talented developers everywhere, and I anticipate a number of AR applications debuting to gamify the world and alter human behavior. Who will come up with the next big AR application? Supplement my ideas below with your own in the comments!

Running with Google Glass and seeing a ghost ahead marking your personal best

Restaurants using AR to highlight secret menu items

Department stores providing a customized visitor experience by visually highlighting sales and new items or making recommendations on what to buy around the store for a camping trip or birthday party

AR showing customers how popular each item in a store has been in the last week, month, and year with a “heat score.” I could also see reviews popping up over items as well.

Zoo and museum curators building interactive exhibits in AR to amaze and educate visitors about animals and topics that would be too expensive or inconvenient to physically bring in-house

Being able to automatically identify people and their education/work history in a networking room

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Sometimes I think Scott Kirsner, Boston’s most prominent and respected tech journalist, has a bi-polar relationship with the Boston tech scene.

Shots Fired

In his most recent piece, titled, “Why Entrepreneurs Still Bolt from Boston,” Kirsner published the musings of a small group of entrepreneurs that left Boston for Silicon Valley. Twitter quickly erupted in a firestorm, with tech leader Mike Volpe advocating for a more even-keeled perspective:

The same rehashed points littered the page: restrictive non-compete laws, weak entrepreneur retention, lack of a betting culture from the angel investing and venture formation perspective, and a deep focus on serving the enterprise while ignoring consumer-facing products. Those arguments have been wrought out in dozens of articles and conversations, and while issues like reforming non-competes are still a black mark on the ecosystem, it’s difficult to complain when Boston’s innovation economy comes from a position of true strength in all these areas.

Add to that foundation the prominence of our educational institutions, diversity of expertise (biotechnology, robotics, healthcare, hardware, big data), and the fact that I overhear conversations on topics other than the next round of fundraising, disruption, achieving unicorn status, and growth hacking at my local watering hole.

It’s a Matter of Perspective

But the article’s implied takeaway? Boston is still a sieve. Our young, budding startup minds are leaving to build the next giants in NYC and the west coast. Silicon Valley envy bleeds through the page with every keystroke. Maybe this BU grad with the cool, bright green wire frame glasses just needs to be re-inspired by the Scott Kirsner of 2011. The guy who resolved to hit pause on comparisons with the Valley, to focus on being great and highlight what makes the tech economy in New England so awesome:

What if we stopped comparing and benchmarking? What if we stopped wondering whether we’re as innovative as New York or Silicon Valley? What if we stopped positing that New England in the 1970s or 1980s might have been more competitive than it is today? Basically, what I’m asking is: what if we put all comparisons on pause for 2011, and just focused on creating companies, solving big problems, and kicking a–?

I confess: I’m more guilty than most when it comes to making comparisons. But I promise that in 2011, I’m not going to give an exit interview to every entrepreneur who leaves Boston because they hope to do better in New York or the Valley, asking them to opine on Boston’s shortcomings. News flash: entrepreneurs can fail in those places too. When I’m at a panel discussion where the panelists start bloviating about the Valley versus Boston, or New York versus Boston, I’m walking out.

And the best part of all this? I think the Silicon Valley envy that seemed pervasive in decades past has finally been cleaned up like the Charles River. After spending the last seven years engrossed in Boston’s innovation ecosystem, I think the region has truly come into its own.

Are Startups Actually Leaving Boston?

Every once and a while, an article will hit the wire about a startup leaving Boston for greener pastures elsewhere. For those who left, it always seemed like a natural progression. My friends at music startup Cymbal recently moved to NYC to avail of a strong music scene…makes sense. And yes, it’s natural to dream wistfully about what would have happened if Mark Zuckerberg, Drew Houston, and Joe Gebbia grew Facebook, Dropbox, and Airbnb in the same region in which they graduated. This all begs the question: are startup departures the exception or the rule?

To test this question, I decided to check in on the 86 startups identified in Kinvey’s Startup map, released in March 2013. How many startups were acquired, died, and continued to grow? More importantly, how many left the region? I did some digging (see bottom of page), and what I found wasn’t surprising:

The Verdict: Boston Startups are Staying in Beantown and Succeeding

2 (3%) moved away (OSComp Systems to Houston and Plastiq to Silicon Valley)

These statistics are incredible, even if some of the startups aren’t still in hyper-growth mode or some of the acquisitions were actually acquihires. The Kinvey data set also erred toward well-known, growing startups at the time of publication. In addition, I did not limit the data set to startups at/near their founding. Regardless of these caveats, we can draw some conclusions:

Startups who begin in Boston typically build their businesses and exit in Boston

The few companies that leave seek the epicenter of their chosen industry

Yes, some exited founders and developers head to Silicon Valley to become investors, engross themselves in the Valley culture, and start/join new ventures. The same can be said of serial entrepreneurs coming to Boston from all over the world to start their next venture.

The Kids are Alright

The comings and goings of entrepreneurs is natural. Boston’s startup culture is different from anywhere else in America, including Silicon Valley, and that’s ok. Founders can and do succeed in Boston even though more venture capital is invested with faster velocity to startups in the Bay Area. The best Boston startups still get funded.

Maybe we overhaul the marketing message, starting with the local tech press. Maybe we put some force behind the “Built in Boston” movement. I don’t believe we have Silicon Valley spite, so let’s embrace our Boston bravado.

Scott, I know these Boston vs. Silicon Valley articles drive some of the highest page view counts each year, but it’s hurting how our startup ecosystem is perceived across the country. You have the loudest microphone in Boston tech, let’s not kill ourselves by a thousand little cuts.

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“This is God View.” Austin Geidt was radiating so much excitement, I thought she was going to slip off her bar stool at Mead Hall in Cambridge, MA. As she scrolled across the Google map of NYC and SF, a few little black car logos were ticking up and down the streets. “I can monitor everything happening on our platform from this one view — which drivers have the app open, which cars have clients in them, which areas aren’t being serviced well enough. One day, there will be thousands of cars on this screen.”

Meeting Travis

The heat on my interview with the relatively unknown 20-person startup called Uber quickly ratcheted up to incinerate. Their Co-Founder and CEO, Travis Kalanick, was in town for business, and he was eager to meet me as a candidate to lead the launch of their Boston office. Riding high off the sale of his peer-to-peer file sharing company Red Swoosh for $19MM, Travis was clearly eager to prove he could swing for the fences with Uber. With $12MM in funding, their expansion plans had begun.

It was a Tuesday night, 8/30/2011, when I sat down with the dark-haired impresario. I prepared for the conversation by playing Kalanick’s interview with Jason Calacanis on loop for a couple hours at the Cosi down the street. We spent the next hour feeling each other out. I grabbed a beer, he ordered a water. We grilled each other on ideal team structure, business models, my experience at LevelUp, and his grand vision for Uber. Having previously used the $50 in credit given to me by Austin to get to the U.S. Open in Flushing, I openly wondered how the average millennial was going to choose a $50 black car ride from Brooklyn to Queens over a short subway ride, and Travis alluded to one day going beyond black cars. The conversation ended with a smile, handshake, and promise to push me forward in the interview process. This could be the beginning of something big.

Before I tell you how it ended, let’s revisit how it all started.

Genesis

A tweet from a close friend of a former colleague, who started using this awesome on-demand car service in SF and NYC, caught my attention.

A couple weeks later, I stumbled upon an article in TechCrunch announcing Uber’s intent to launch in Chicago, Seattle, Boston, NYC, and DC. Two years into my tenure at LevelUp, I had no intention to leave. I was a top performing sales rep about to lead the mobile payment startup’s expansion from Boston and Philadelphia to eight cities across the country. Most startup workers would die for the opportunity. But still, I was intrigued.

The Cover Letter

Dear Garrett, Travis, and Ryan,I’m a hardcore Bostonian. I eat Boston (think uBurger), drink Boston (think Stoddards), and live Boston (think Blue Man Group without the face paint and percussion skills). I grew up in a nearby suburb and studied Economics at Tufts University. Many late nights were spent gazing at the city skyline from the rooftop of the Tufts library plotting how I would take Boston by storm. After following your successes in California and New York, I am quickly realizing that the storm is a hurricane, and that hurricane is Uber.I’m a thoroughbred startup guy. I started the Beanie Baby Newsletter in middle school and 80/20 Booksellers in college. After spending my second summer of law school building TapInko at the Dreamit Ventures accelerator, I knew I was destined for startupland. I spent the last 18 months growing SCVNGR from 15 to 70 employees, driving over $100,000 in sales over 6 months while managing the brand new SCVNGR Conferences vertical, leading a team of 8 to go live with over 400 local businesses on SCVNGR rewards, and debuting SCVNGR’s Levelup pilot in Philadelphia with top quality merchants.

I’m loud. I thrive on building both local excitement and national awareness for products and services. At Harvard Square’s MayFair last Sunday, my marketing team and I took home over 800 email addresses for LevelUp Boston and a nasty sunburn after only 5 hours. I embrace guerrilla marketing tactics at conferences and fairs as much as I enjoy speaking at events like AMPSummit, NokiaTalk, MobileMIT, Wharton BizTech, Geoweb Summit, and the upcoming Nordic AppWorks Conference in Oslo, Norway.

I love taking brand new products to a fresh market, especially products that I can get excited about. I’m enamored by Uber’s disruptive model. Bostonians have been waiting for the Uber solution to get them home from the theater district after a hot Saturday night date, from the financial district after a big interview, and from Fenway after a Sox game. Boston is my home, and I would feel privileged to be considered for the Boston City Manager position at your incredible startup.I look forward to hearing from you soon.

Best regards, John Valentine

The Interview Process

It didn’t take long for me to get engrossed in their interview process. First, I had to answer a few questions for Athena Maikish about how Uber should go about dominating Boston. the next week, I was given an Excel challenge in which I had to draw conclusions and make recommendations based on a data set from a number of days worth of rides in NYC. After a 1-hour VLOOKUP refresher course on YouTube, I sat in the lobby of the Sheraton Philadelphia and cranked out charts and graphs to make sense of the huge data set.

I wasn’t the first applicant to tackle the Excel challenge, and as I started poking around I heard disappointing tales from a bunch of people I knew that had failed to pass through the data gauntlet. Fortunately, I made it through.

Having received the green light to start salary negotiations, I spent the next week in NYC taking calls with Travis and Ryan Graves in between pitching restauranteurs to launch on LevelUp’s mobile payment platform. Boston’s launch date was set. My salary was set. My equity package was negotiated. All that was left to do was sign the employment agreement and put in my two weeks notice.

I asked LevelUp’s COO and my good friend Michael Hagan to Sunday brunch the day before my decision was due. Michael couldn’t contain his excitement about LevelUp’s 8-city expansion, and extolled the virtues of being a part of something special from the beginning through massive scale. Either way though, he would respect my decision. “Michael, if I show up tomorrow at work at 9am, I’m in. If not, I’m out.”

The Goodbye Letter

Ryan, Travis, Athena, and Austin,

First of all, I’d like to thank all of you for taking me through your interview process, challenging me, and putting in time and effort to determine whether I was a good fit for your team. I’m convinced that I would work incredibly with all of you, and that we would make Boston a special city for Uber.

But there’s this thing called LevelUp. I’ve been with the startup through its ups and downs, twists and turns, good pivots and bad. If you had pushed me through the interview process at the outset (while LevelUp was experimenting with deals) the decision to jump would have been much easier. At its current state, LevelUp is sitting at the calm before next week’s rapid expansion, much like Uber was a few months back. I am one of the two linchpins for the expansion.

While I’d certainly have a major role in Uber’s success immediately in Boston and in other capacities down-the-line, the ability to both open and later manage a portfolio of cities for the company I helped grow will not only give me upside monetarily, but more importantly allow me to make macro decisions that move entire company.

Before falling asleep last night I asked myself where my heart was, and I chose LevelUp. It’s where my heart is right now.

I know you’re going to dominate here in Boston. Think Seattle x2. Good luck in finding the elusive GM for Boston and the rest of your cities. Another good fit is certainly out there. We like to think we’re pretty sharp here in Beantown.

Cheers, John

The Aftermath

I spent the next three years building upon my successful tenure at LevelUp. We did launch those eight cities, and I spent almost two years building out our restaurant network with 25 of the best salespeople I’ve ever known. I wouldn’t trade those flights, strategy meetings, customer service visits, announcements, and team dinners for anything in the world. Towards the end of my time with LevelUp, we expanded to build custom mobile payment and loyalty apps for mid-size and national brands. I went out on top, with very little left to prove.

I knew Uber was going to be successful, but few at the time could have predicted its meteoric rise. Michael Pao took the Boston GM position, crafted “surge pricing,” and just left to be an EIR at Greylock. Uber went on to raise over $10B over 14 rounds of funding, most recently with a valuation of $62.5B. Contingent on my staying at Uber through full vesting and their valuation holding strong or growing, I would have been staring at stock certificates worth tens of millions of dollars. Unfathomable amounts of money.

The Lesson

Life is like one of those “Choose Your Own Adventure” books you read as a kid. Every big decision is a fork in the road. You make a gut call and flip to page 35. The only difference is, in life, there is no peeking or turning back.

For every Uber, there are thousands of other startups that simply tread water or sink under the weight of a bad team, terrible business strategy decisions, or superfluous funding. Did I get hit with little pangs of second-guessing with each funding announcement to hit TechCrunch? Yea, definitely. Did my first dozen Uber rides around Boston sting a little bit? Sure. Did it fade over time? Yep. Am I the only person that has ever missed a lottery ticket like this? Hell no.

For every missed opportunity in my life, there have been hundreds of great decisions. Like joining a small startup called SCVNGR founded by an 18-year-old wunderkind with a $500,000 check from Highland Capital. Like marrying the woman of my dreams surrounded by incredible friends and family. Like recently joining MassChallenge, one of the few organizations to dream of a worldwide startup renaissance and have a damn good chance of actually making happen. Instead of hustling with one startup, my work has a daily impact on hundreds. It’s a beautiful thing.

For all those agonizing over your next big decision or lamenting a missed opportunity, you are only on page 20 of a thousand page story.

Like this:

It was the time of night when the Bernie the cockapoo and Fernando the chihuahua are curled up in their beds, Michelle is chopping vegetables for our little Chinese New Years Eve gathering, and I’m finishing up a couple work emails that I take a moment to reflect on how lucky I am. Lucky to be healthy. Lucky to be happy. Lucky to be surrounded by people I enjoy hanging with. Lucky in love.

Now look, I’m only 30. I have lived far less than half the average American male lifespan, but I feel like I’m overflowing with advice for young twenty-somethings trying to make their way in the world. I’ve been there. Done that. Seen myself, colleagues, friends, peers, and family celebrate success, trip and fall, witness marriages, deal with pain, excitement, depression, divorce, and elation. Life is full of it.

Along the way, I have developed a stupid simple way for someone to determine whether they are ready to “pop the question.” I implore you to take these basic principles with a grain of salt. My hope is that everyone finds a nugget of truth to keep in the back of their minds when going through the excitement and stress of the courting process. I present to you…the basic principles of the proposal.

Don’t propose before you and your intended turn 25

People change all through their lives, it’s a truism. Their tastes change, allergies change, likes and dislikes change, The years between 21 and 25 are when young people are entering the workforce, striking out on their own, figuring out how the world works, dating, getting hurt, feeling guilty about mistakes, and starting their career. After conferring with my friends, I believe 25 is the year of most incredible highs and lows. Make sure you know who you are before professing undying love to another.

Make sure you go through three life changes together before proposing

These life changes could be exciting changes like a job promotion, moving in together, marriage in the family, moving to a new city, changing jobs, or going to grad school. The changes could be negative like death or illness in the family, getting laid off, or having money issues. If you haven’t been through three highs and lows as a couple, there is no knowing how you would react. You’re marrying this person for life…you need to make sure they’ll hold your hand on the roller coaster.

Don’t propose before two years of dating has passed, and don’t wait until after three years

Before you propose remember: you will be spending the rest of your life with this person. Are you cool with that? Have you spent enough time with that person to verify they’re the one? I feel like two years of dating is enough to give people a true green or red light on the proposal front. Two years is needed to persevere through the three life changes detailed above, but also to enjoy dating life together. Once you’re married, you won’t be “just dating” ever again. Each stage of life is meant to be savored, so enjoy the dance. If you’re thinking about proposing out of fear your girlfriend or boyfriend might leave you, you both aren’t ready to make the lifetime commitment.

Just as proposing before two years have passed feels too soon, waiting until after three years of dating to propose if simply leading your intended on. C’mon man! If you don’t know whether they’re the one, shit or get off the pot! Respect their feelings…if they are looking to find a partner and you’re unsure after three years, you need to set them free. It’s not fair to either of you. An exception to this rule are those couples who started dating in college or their early twenties. If things are still rocking at three years, keep it going until you hit 25. At that point, feel free to drop the diamond at any point. There are also other exceptions I have seen like military and education intervention. You know the drill.

What I’m really trying to say is, enjoy every stage of your life and don’t rush things. Just because the Millennial generation isn’t getting married at the same clip of our predecessors doesn’t mean we have to eschew is altogether. And on the other hand, there is no rush to jump into a lifelong commitment. I’m just bringing a wee bit of science to the art of love.

Like this:

This winter, after five years of helping build LevelUp into the strong mobile payments player they are today, I decided to embark on a new challenge with Swipely.

It wasn’t an easy decision. I had complete mastery over LevelUp’s enterprise offering, we were coming off our best enterprise sales quarter ever, I had built strong personal relationships with the team through failures, pivots, and successes, and this year would be one of seismic shifts and excitement in the mobile payments space.

And yet, I made the jump confidently and landed with two feet in a fast-growing payments and analytics startup that is instilling within me the methods of their success and is eager to tap my experience to grow their national division. This next phase will be incredibly exciting and challenging. Following the advice of Nietzsche, “build your cities on the slopes of Vesuvius. Send your ships into uncharted seas.”

The job change decision-making process is incredibly complex, and it’s difficult to create a model for yourself let alone an entire category of job-seekers. There are a number of open positions available in most job categories in major metros, so which startups should you pursue? My company search criteria soon became a hybrid of startup DNA and values I developed myself and others I adopted from investors I admire.

In many ways, startup workers are like venture capitalists. Investors are looking for the classic triple-threat of team, market size, and product. The end-game for investors is cashing out on the other side with a 10x win. Startup workers are looking for the next rocketship product to build or sell, so why not follow the venture investment model to make your decision? Check out my tech job search criteria below:

Paul Graham has become famous for this motto, which has become something of ultimate aspiration for the young guns at YCombinator. But PG has a point. A company can only go so far on enthusiasm and confidence. Great companies build something a large number of people want a small amount or something a small number of people want a large amount. The best products spread through word-of-mouth recommendations and referrals.

The CEO works harder/longer than everyone at the company + can magically see six months further into the future than the competition

A long time ago when I was right out of undergrad, I worked for a startup in which the CEO came to work late every day, played techno music for a few hours, blasted out some emails, and left with everyone else. Startups need a leader who instills a high level of confidence in their team, someone who will hold the company’s torch high during periods of extreme stress and setbacks and also great victory. Industries are changing quickly because of technological disruption, and leaders who have the foresight to see where their category is shifting will put their startup in the best position to win. A little weirdness doesn’t hurt either!

The startup has momentum

VCs aren’t looking to invest in companies with linear growth, and startup workers aren’t geared to want to work for them either. Borrowing a bit from Mark Suster, many of the best companies have seen encouraging levels of traction. Significant growth in the number of paying customers, top line revenue, users, and channel partners drive VC checkbooks out of pockets and hordes of prospective employees to a company’s door.

The startup boasts a top-flight roster

People. People. People. It’s easier to put your fist through a brick wall than get VC funding without a stellar team. The same should apply for startup workers in the job hunt. A product might seem to be growing like a weed, but 9 times out of 10 a well-executing team made it hum. There is no easier way to build self-motivation and enthusiasm for your job than being surrounded with intelligent, driven co-workers. Make sure your interview process includes conversations with prospective colleagues and members of other departments you’ll be interacting with on a weekly basis. Just as you are the average of your five best friends, you are the average of your five closest colleagues.

A huge potential market awaits

Pass the Kool-Aid. If you’re looking to be a part of a hyper-growth company, the executive team must have their sights set on a large market opportunity. Small markets turn startups into lifestyle businesses or services companies that produce singles and doubles, not home runs. But don’t be fooled into thinking a startup is going after a small market due to their current go-to-market strategy…they may have bigger ambitions and pivots planned. Do your diligence and ask questions about the company’s 2-year product and positioning trajectory.

You have subject matter proficiency

Investors love to put money to work in fields they know. Having intimate knowledge of an industry and its competitors makes a VC more valuable as a trusted advisor. A startup worker with industry experience and insight can more quickly assimilate into an organization’s culture and help chart the path forward.

How much risk are you willing to take on in your job search? The answer to that question will determine whether you’re an angel investor, apt to go for more risky opportunities with higher potential reward, or a Series A, B, C, or D venture capitalist, choosing to work for companies with more longevity and de-risking under their belt. There is no one size fits all criteria, and everyone will think about the challenge differently. Just promise me you’ll do your diligence.